Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour

Discover Chicago’s 1920s Speakeasy Scene for a Private 3-Hour VIP Experience

The Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour offers a captivating journey back to the Roaring Twenties, where Chicago’s underground nightlife thrived during Prohibition. For $950 per group of up to five people, this tailored experience combines history, secret entrances, and classic cocktails in a luxurious setting. The tour lasts 3 hours and features 3 to 4 historic speakeasies, many still in their original condition.

This tour is perfect for those looking for an intimate, behind-the-scenes look at Chicago’s clandestine drinking culture. Led by a young, knowledgeable local historian, the experience is both fun and educational, with a focus on the stories of gangsters, bank robbers, and bootlegging that defined the era. Travelers should note that alcohol is available for purchase at each stop, and the tour requires some mobility, not suited for those with physical impairments.

You can check availability for your dates here:

Key Points

• Private group experience for up to 5 people with luxury transportation
• Includes access to 3-4 historic speakeasies, many with original features
• Led by a young, expert guide skilled in Chicago’s Prohibition history
• Cost: $950 for the entire 3-hour tour, with hotel pickup and drop-off
• Alcoholic drinks are available for purchase at each venue
• Tour is not suitable for guests under 21 or those with mobility issues

Exploring Chicago’s Secret Speakeasies in Style

The tour begins with hotel pickup within Chicago city limits, where travelers are chauffeured in a luxury vehicle such as a Mercedes S 550 Sedan, Cadillac Escalade, Mercedes Sprinter, or Mini Coach Bus, depending on the group size. This luxury transportation sets a tone of exclusivity, easing the transition between stops and adding to the VIP feel of the experience.

Once on the road, your guide, who is well-versed in Chicago’s history, starts sharing stories of the city’s Prohibition era, including tales of gangsters, racketeering, and bootlegging. The journey itself feels like stepping into a 1920s gangster movie, with visits to hidden entrances and secret passages that connect to vintage speakeasies.

Inside Chicago’s Authentic Speakeasies

Each of the 3 to 4 speakeasies visited during the tour is a piece of history. Many of these venues have preserved their original decor and atmosphere, offering an authentic glimpse into the past. The guides recommend Prohibition-era cocktails that were favorites of Chicago’s infamous gangsters and bank robbers, adding a flavorful layer to the storytelling.

Guests can purchase classic cocktails, such as gin rickeys or whiskey smashes, at each stop. The guides are happy to suggest drink options aligned with the era, enhancing the feeling of being part of a secret society. These venues often have a small, intimate vibe, ideal for enjoying a drink while listening to stories of Chicago’s unruly past.

The Skill of the Young, Local Guide

A standout feature of this tour is the guide’s expertise and storytelling ability. Described as knowledgeable, friendly, and accommodating, guides like Alan and Kai make the experience engaging and personalized. They are skilled at adapting the tour to guests’ interests, whether focusing more on historical gangster tales or the speakeasy ambiance.

The guides’ storytelling keeps the tour lively and informative, making complex history accessible and entertaining. Their familiarity with Chicago’s underground nightlife helps uncover hidden stories that many might not encounter through books or casual visits.

More Great Tours Nearby

Comfortable and Flexible Transport Options

The luxury transportation is a key part of the VIP experience. Depending on group size, the vehicle ranges from a Mercedes S 550 Sedan to a full-sized Mini Coach Bus. The chauffeur gratuity is included, ensuring a smooth, hassle-free ride.

This transport setup allows travelers to relax between stops and enjoy the city sights in style. The hotel pickup and drop-off service makes the outing seamless, avoiding the need for public transport or walking long distances.

Specific Venues and Their Unique Features

The speakeasies visited during the tour often maintain their original 1920s decor, creating an immersive environment. These venues are still operational, and their interiors reflect the glamour and secrecy of the Prohibition era. Many of these locations have historic significance, being venues that gangsters and bank robbers frequented nearly a century ago.

Guests can expect to see hidden entrances, secret tunnels, and vintage furnishings that transport them back in time. The combination of preserved architecture and authentic cocktails enhances the overall experience.

Practical Details and Booking Info

The tour is private, allowing for an intimate experience tailored to the group. Reservations can be made with flexible payment options, including the ability to reserve now and pay later. Cancellations are free up to 24 hours in advance, providing peace of mind.

Guests should bring passport or ID, and driver’s license, as these might be required for entry or verification. The tour does not accommodate guests with mobility issues or those under 21 years of age.

Who Will Enjoy This Tour Most?

This tour appeals most to history buffs, mixture of fun and educational experiences, and those curious about Chicago’s gangster past. It’s ideal for small groups of up to five, seeking a luxurious, personalized adventure. If you appreciate storytelling, vintage decor, and a lively atmosphere, this tour delivers.

However, guests should be aware that alcohol is for purchase only, and the tour pace involves some walking and vehicle stops. It’s best suited for adults interested in history and nightlife.

Final Thoughts on the Chicago Speakeasy VIP Tour

The 3-hour private speakeasy tour offers a luxury glimpse into Chicago’s Prohibition-era underground nightlife. Led by knowledgeable guides, it balances entertainment with education, making it a compelling choice for visitors wanting an exclusive experience.

While it might not be suitable for everyone—especially those with mobility challenges or under 21—it provides a memorable and personalized journey through Chicago’s secret past. The luxury transport and private setting ensure a comfortable and flexible adventure, perfect for small groups looking for something special.

Frequently Asked Questions

Are alcoholic beverages included in the tour?
No, alcohol is not included in the tour price but is available for purchase at each speakeasy. The guides also offer drink recommendations aligned with the Prohibition era.

What is the group size for this tour?
The private tour accommodates up to 5 people, making it ideal for small groups or families seeking a personalized experience.

Is this tour suitable for guests with mobility issues?
No, this experience is not suitable for guests with mobility impairments due to the nature of venue access and walking involved.

Can I cancel or reschedule?
Yes, free cancellation is available up to 24 hours before the scheduled tour. You can also reserve now and pay later to keep your plans flexible.

What should I bring on the tour?
Guests should carry passport or ID and driver’s license. Sleeveless shirts are not allowed at the venues, so plan your clothing accordingly.

You can check availability for your dates here: More Great Tours Nearby